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Molecules 2012, 17(4), 3969-3980; doi:10.3390/molecules17043969
Article

Synthesis and Herbicidal Activity Evaluation of Novel β-Carboline Derivatives

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Received: 15 February 2012; in revised form: 15 March 2012 / Accepted: 22 March 2012 / Published: 2 April 2012
(This article belongs to the Section Organic Synthesis)
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Abstract: Based on the original structure of harmine, several novel 1,2,3,4-tetrahydro-β-carboline, β-carboline and 1-substituted-β-carboline derivatives bearing a substituted carbohydrazide group at C-3 were designed and synthesized to investigate the structure-activity relationship of their analogues. All of the compounds were characterized by infrared (IR), proton and carbon nuclear magnetic resonance (1H-NMR, 13C-NMR), and mass spectroscopy (MS). The bioassay tests showed that N'-benzylidene-1-phenyl-β-carboline-3-carbohydrazide (C25H18N4O, m.w. 390.4) (c2) and N'-(4-trifluoromethyl-benzylidene)-1-phenyl-β-carboline-3-carbohydrazide (C26H17N4OF3, m.w. 458) (d2) exhibited good inhibitory activity against dicotyledonous and monocotyledonous weeds, with EC50 values of 4.83 µM and 14.25 µM, respectively.
Keywords: N'-substituted-1,2,3,4-β-tetrahydro-β-carboline-3-carbohydrazide; β-carboline; N'-substituted-β-carboline-3-carbohydrazides; 1-substituted-β-carboline-3-carbohydrazides; herbicidal activity N'-substituted-1,2,3,4-β-tetrahydro-β-carboline-3-carbohydrazide; β-carboline; N'-substituted-β-carboline-3-carbohydrazides; 1-substituted-β-carboline-3-carbohydrazides; herbicidal activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Weng, Q.; Huang, J.; Zeng, Y.; Deng, Y.; Hu, M. Synthesis and Herbicidal Activity Evaluation of Novel β-Carboline Derivatives. Molecules 2012, 17, 3969-3980.

AMA Style

Weng Q, Huang J, Zeng Y, Deng Y, Hu M. Synthesis and Herbicidal Activity Evaluation of Novel β-Carboline Derivatives. Molecules. 2012; 17(4):3969-3980.

Chicago/Turabian Style

Weng, Qunfang; Huang, Jingfei; Zeng, Yong; Deng, Yueye; Hu, Meiying. 2012. "Synthesis and Herbicidal Activity Evaluation of Novel β-Carboline Derivatives." Molecules 17, no. 4: 3969-3980.


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